Methylthiomethyl esters as flavor additives

Abstract

Methylthiomethyl esters of aliphatic acids have been found useful in imparting or enhancing flavors in foodstuffs. They are particularly useful with respect to fruit and berry flavors.

What we claim and desire to protect by Letters Patent is: 
     
       1. A fruit or berry flavoring composition or a fruit or berry flavor-enhancing composition comprising a combination of olfactorily active ingredients including at least one methylthiomethyl ester having the structural formula R--COOCH 2  --S--CH 3  wherein R is selected from the class consisting of hydrogen, alkyl radicals with 2 to 9 carbon atoms, alkenyl radicals with 2 to 9 carbon atoms, and polyunsaturated radicals with 4 to 9 carbon atoms and at least one compound selected from the class consisting of: orange oil   isoamyl acetate   phenyl ethyl isovalerate   fusel oil   damascenone   lie de vin   ethyl maltol   2-methyl butanol   2-methylbutyric acid   phenylethyl alcohol   angelica root oil   trans-2-hexenol   buchu oil   methyl anthranilate   cognac oil   2-methyl-2-pentenoic acid   petitgrain oil   vanillin   cedar leaf oil   maltol   isoamyl isovalerate   benzyl alcohol   methyl butyrate   linaolool   isobutyl acetate   isoamyl butyrate   methyl isobutyl carbinyl acetate   ethyl acetate   ethyl butyrate   ethyl benzoate   ethyl hexanoate   citral   ethyl heptanoate   cuminic aldehyde   cis-3-hexenol   beta-ionone   ethyl isovalerate   tangerine oil   phenyl butyrate   benzyl acetate   amyl acetate   orange peel oil   geranyl acetate   bergamot oil   gamma-nonalactone   lime oil   Ylang Ylang   orange terpenes   beta-terpineol   methyl cinnamate.   
     
     
       2. A flavoring composition according to claim 1 wherein R is hydrogen or an alkyl radical with 1 to 9 carbon atoms. 
     
     
       3. The flavoring composition according to claim 2 wherein the ester is methylthiomethyl butyrate. 
     
     
       4. The flavoring composition according to claim 2 wherein the ester is methylthiomethyl isobutyrate. 
     
     
       5. The flavoring composition according to claim 2 wherein the ester is methylthiomethyl 2-methylbutyrate. 
     
     
       6. The flavoring composition according to claim 2 wherein the ester is methylthiomethyl valerate. 
     
     
       7. The flavoring composition according to claim 2 wherein the ester is methylthiomethyl isovalerate. 
     
     
       8. The flavoring composition according to claim 2 wherein the ester is methylthiomethyl hexanoate. 
     
     
       9. The flavoring composition according to claim 2 wherein the ester is methylthiomethyl heptanoate. 
     
     
       10. The flavoring composition according to claim 2 wherein the ester is methylthiomethyl octanoate. 
     
     
       11. A flavoring composition according to claim 1 wherein R is an alkenyl radical with 2 to 9 carbon atoms. 
     
     
       12. The flavoring composition according to claim 11 wherein the ester is methylthiomethyl tiglate. 
     
     
       13. The flavoring composition according to claim 11 wherein the ester is methylthiomethyl 2-hexenoate. 
     
     
       14. The flavoring composition according to claim 11 wherein the ester is methylthiomethyl 2-methyl-2-pentenoate. 
     
     
       15. A flavoring composition according to claim 1 wherein R is a polyunsaturated alkyl radical with 4 to 9 carbon atoms. 
     
     
       16. The flavoring composition according to claim 15 wherein the ester is methylthiomethyl lavandulate. 
     
     
       17. A foodstuff to which has been added about 0.1 to 5 parts per million, based on the total weight of said foodstuff, of at least one methylthiomethyl ester having the structural formula R--COOCH 2  SCH 3  wherein R is selected from the class consisting of hydrogen, alkyl radicals with 1 to 9 carbon atoms, alkenyl radicals with 2 to 9 carbon atoms and polyunsaturated alkyl radicals with 4 to 9 carbon atoms. 
     
     
       18. A foodstuff according to claim 17 wherein R is hydrogen or an alkyl radical with 1 to 9 carbon atoms. 
     
     
       19. The foodstuff of claim 18 wherein the ester is methylthiomethyl butyrate. 
     
     
       20. The foodstuff of claim 18 wherein the ester is methylthiomethyl isobutyrate. 
     
     
       21. The foodstuff of claim 18 wherein the ester is methylthiomethyl 2-methylbutyrate. 
     
     
       22. The foodstuff of claim 18 wherein the ester is methylthiomethyl valerate. 
     
     
       23. The foodstuff of claim 18 wherein the ester is methylthiomethyl isovalerate. 
     
     
       24. The foodstuff of claim 18 wherein the ester is methylthiomethyl hexanoate. 
     
     
       25. The foodstuff of claim 18 wherein the ester is methylthiomethyl heptanoate. 
     
     
       26. The foodstuff of claim 18 wherein the ester is methylthiomethyl octanoate. 
     
     
       27. A foodstuff according to claim 17 wherein R is an alkenyl radical with 2 to 9 carbon atoms. 
     
     
       28. The foodstuff of claim 27 wherein the ester is methylthiomethyl tiglate. 
     
     
       29. The foodstuff of claim 27 wherein the ester is methylthiomethyl 2-hexenoate. 
     
     
       30. The foodstuff of claim 27 wherein the ester is methylthiomethyl 2-methyl-2-pentenoate. 
     
     
       31. A foodstuff according to claim 17 wherein R is a polyunsaturated alkyl radical with 4 to 9 carbon atoms. 
     
     
       32. The foodstuff of claim 31 wherein the ester is methylthiomethyl lavandulate. 
     
     
       33. A method of improving the flavor of a foodstuff which comprises adding thereto about 0.1 to 5 parts per million of at least one methylthiomethyl ester having the structural formula R--COOCH 2  SCH 3  wherein R is selected from the class consisting of hydrogen, alkyl radicals with 1 to 9 carbon atoms, alkenyl radicals with 2 to 9 carbon atoms and polyunsaturated alkyl radicals with 4 to 9 carbon atoms.